Financial Freedom with Real Estate Investing

24 Nov 2025 06:00

MB499: Swap Till You Drop: Building Wealth with Tax-Advantaged Real Estate – With Louis Rogers

What if you could build wealth through real estate… without paying taxes along the way? In this episode, Michael Blank welcomes Louis Rogers, founder of Capital Square and pioneer of the tenants-in-common model still widely referenced today. Lewis breaks down the simplicity of 1031 exchanges, why DSTs have replaced TICs, and how investors can eventually move into a REIT structure to enjoy completely passive investing — while still deferring taxes. If you want to learn how the wealthy use the tax code to accelerate their net worth, this episode is a must-listen.

Key Takeaways:

1031 exchanges are simpler than most people think — and typically cost about $1,000 using a qualified intermediary.
The old tenants-in-common (TIC) structure is obsolete — DSTs are now the preferred option for 1031 investors.
Investors can move from active ownership → DSTs → UPREIT, getting more passive over time.
Tax deferral can continue for life — with a step-up in basis eliminating capital gains upon inheritance.
The U.S. tax code is uniquely favorable to real estate — wealthy families use it strategically.
Paying taxes is a choice: learn the rules and keep more of your money working for you.